Microsoft has informed IT administrators of potential connection challenges users may face with the Always On VPN following the installation of the September 2026 Windows 11 security updates. This remote access solution, designed to supersede the older DirectAccess technology, is compatible with a variety of devices, including those that are domain-joined, non-domain-joined, and Microsoft Entra ID–joined.
Always On VPN operates unobtrusively in the background, establishing a secure connection to the corporate network automatically whenever a device accesses the internet. This solution not only allows administrators to specify which applications and services can utilize the VPN connection but also supports contemporary VPN protocols such as IKEv2 and SSTP, alongside multi-factor authentication (MFA) to enhance security measures.
Connection Issues and Workarounds
In a service alert reported by BleepingComputer and shared by Microsoft MVP Susan Bradley, the tech giant indicated that users might encounter difficulties when attempting to connect to their organization’s enterprise network via Always On VPN. Microsoft elaborated that these issues could arise if the VPN is set to automatically attempt an alternative connection method upon initial failure, particularly when employing automatic protocol selection with IKEv2 and SSTP.
Symptoms of the problem may include VPN connections remaining in a ‘Connecting’ state or repeatedly attempting to establish a connection without success. Users might also see the error message: ‘The specified port is already in use.’
| Affected Versions | Originating Update |
|---|---|
| Windows 11, version 26H1 | KB5124012 |
| Windows 11, version 25H2 | KB5124008 |
| Windows 11, version 24H2 | KB5124008 |
While Microsoft is actively working towards a permanent resolution, the company has provided a temporary workaround for affected users. IT administrators can alleviate the issue by adjusting the Always On VPN profile from automatic protocol selection to a single protocol—either SSTP or IKEv2—tailored to their specific environment and configuration needs.
Organizations are encouraged to select the protocol based on their unique environment, security requirements, and deployment strategies. This month’s cumulative updates have also been associated with various other issues impacting both home and enterprise Windows users.
Recently, Microsoft released emergency updates to address problems related to Hyper-V, Remote Desktop Services, and USB audio, all of which were triggered by the September 2026 updates. Additionally, a temporary workaround was provided for a separate issue preventing some Windows 11 users from logging in with valid domain credentials. The company is also addressing another bug that may disrupt the functionality of the built-in File History backup feature in Windows.
